Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

Amos B. Smith; B. Scott Freeze; Matthew J. LaMarche; Tomoyasu Hirose; Ignacio Brouard; Paul V. Rucker; Ming Xian; Kurt F. Sundermann; Simon J. Shaw; Mark A. Burlingame; Susan Band Horwitz; David C. Myles

doi:10.1021/ol047686a

Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

Amos B. Smith
, B. Scott Freeze
, Matthew J. LaMarche
, Tomoyasu Hirose
, Ignacio Brouard
, Paul V. Rucker
, Ming Xian
, Kurt F. Sundermann
, Simon J. Shaw
, Mark A. Burlingame
, Susan Band Horwitz
, David C. Myles

Molecular Pharmacology

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

(Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

Original language	English (US)
Pages (from-to)	311-314
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/ol047686a
State	Published - Jan 20 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol047686a

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title = "Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide",

abstract = "(Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.",

author = "Smith, \{Amos B.\} and Freeze, \{B. Scott\} and LaMarche, \{Matthew J.\} and Tomoyasu Hirose and Ignacio Brouard and Rucker, \{Paul V.\} and Ming Xian and Sundermann, \{Kurt F.\} and Shaw, \{Simon J.\} and Burlingame, \{Mark A.\} and Horwitz, \{Susan Band\} and Myles, \{David C.\}",

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doi = "10.1021/ol047686a",

language = "English (US)",

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T1 - Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

AU - Smith, Amos B.

AU - Freeze, B. Scott

AU - LaMarche, Matthew J.

AU - Hirose, Tomoyasu

AU - Brouard, Ignacio

AU - Rucker, Paul V.

AU - Xian, Ming

AU - Sundermann, Kurt F.

AU - Shaw, Simon J.

AU - Burlingame, Mark A.

AU - Horwitz, Susan Band

AU - Myles, David C.

PY - 2005/1/20

Y1 - 2005/1/20

N2 - (Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

AB - (Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

UR - https://www.scopus.com/pages/publications/13444291392

UR - https://www.scopus.com/pages/publications/13444291392#tab=citedBy

U2 - 10.1021/ol047686a

DO - 10.1021/ol047686a

M3 - Article

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AN - SCOPUS:13444291392

SN - 1523-7060

VL - 7

SP - 311

EP - 314

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

Abstract

ASJC Scopus subject areas

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